RU2560877C2 - Способ получения глицидиловых эфиров разветвленных монокарбоновых кислот - Google Patents
Способ получения глицидиловых эфиров разветвленных монокарбоновых кислот Download PDFInfo
- Publication number
- RU2560877C2 RU2560877C2 RU2014102706/04A RU2014102706A RU2560877C2 RU 2560877 C2 RU2560877 C2 RU 2560877C2 RU 2014102706/04 A RU2014102706/04 A RU 2014102706/04A RU 2014102706 A RU2014102706 A RU 2014102706A RU 2560877 C2 RU2560877 C2 RU 2560877C2
- Authority
- RU
- Russia
- Prior art keywords
- monocarboxylic acid
- reaction
- acid
- aliphatic monocarboxylic
- aliphatic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 63
- 150000002763 monocarboxylic acids Chemical class 0.000 title claims description 14
- IWYRWIUNAVNFPE-UHFFFAOYSA-N Glycidaldehyde Chemical class O=CC1CO1 IWYRWIUNAVNFPE-UHFFFAOYSA-N 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 61
- -1 glycidal ester Chemical class 0.000 claims abstract description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 238000001816 cooling Methods 0.000 claims abstract description 11
- 238000004821 distillation Methods 0.000 claims abstract description 10
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 9
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract description 9
- 239000011541 reaction mixture Substances 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 150000003944 halohydrins Chemical class 0.000 claims abstract description 6
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims abstract description 5
- 150000008041 alkali metal carbonates Chemical class 0.000 claims abstract description 5
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 5
- 238000005859 coupling reaction Methods 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 150000004714 phosphonium salts Chemical class 0.000 claims abstract description 3
- 150000004820 halides Chemical class 0.000 claims description 46
- 239000002904 solvent Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 238000009739 binding Methods 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 239000002815 homogeneous catalyst Substances 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 abstract description 22
- 239000003513 alkali Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 150000001350 alkyl halides Chemical class 0.000 abstract 6
- 150000005325 alkali earth metal hydroxides Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 64
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 22
- 239000000047 product Substances 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 10
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 238000007363 ring formation reaction Methods 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- XMKDPSQQDXTCCK-UHFFFAOYSA-N 2,4-dimethylpentanoic acid Chemical compound CC(C)CC(C)C(O)=O XMKDPSQQDXTCCK-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-BYPYZUCNSA-N 2-Methylbutanoic acid Natural products CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 1
- PKJSRUTWBDIWAR-UHFFFAOYSA-N 2-ethyl-2,5-dimethylhexanoic acid Chemical compound CCC(C)(C(O)=O)CCC(C)C PKJSRUTWBDIWAR-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- YRRFBANPGRXQNJ-UHFFFAOYSA-M acetyl(trimethyl)azanium;bromide Chemical compound [Br-].CC(=O)[N+](C)(C)C YRRFBANPGRXQNJ-UHFFFAOYSA-M 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000011021 bench scale process Methods 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NNBFNNNWANBMTI-UHFFFAOYSA-M brilliant green Chemical compound OS([O-])(=O)=O.C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NNBFNNNWANBMTI-UHFFFAOYSA-M 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 1
- OZCWUNHGNVXCCO-UHFFFAOYSA-N oxiran-2-ylmethyl hydrogen carbonate Chemical class OC(=O)OCC1CO1 OZCWUNHGNVXCCO-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09075264.3 | 2009-06-11 | ||
| EP09075264A EP2261220A1 (en) | 2009-06-11 | 2009-06-11 | Process for preparing glycidyl esters of branched monocarboxylic acids |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012100273/04A Division RU2515897C2 (ru) | 2009-06-11 | 2010-06-02 | Способ получения глицидиловых эфиров разветвленных монокарбоновых кислот |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2014102706A RU2014102706A (ru) | 2015-06-27 |
| RU2560877C2 true RU2560877C2 (ru) | 2015-08-20 |
Family
ID=41100757
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014102706/04A RU2560877C2 (ru) | 2009-06-11 | 2010-06-02 | Способ получения глицидиловых эфиров разветвленных монокарбоновых кислот |
| RU2012100273/04A RU2515897C2 (ru) | 2009-06-11 | 2010-06-02 | Способ получения глицидиловых эфиров разветвленных монокарбоновых кислот |
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| RU2012100273/04A RU2515897C2 (ru) | 2009-06-11 | 2010-06-02 | Способ получения глицидиловых эфиров разветвленных монокарбоновых кислот |
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| RU (2) | RU2560877C2 (enExample) |
| TW (1) | TWI405758B (enExample) |
| WO (1) | WO2010142396A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2476672A1 (en) | 2010-12-22 | 2012-07-18 | Momentive Specialty Chemicals Research Belgium S.A. | Glycidyl esters of alpha , alpha branched acids compositions |
| EP2474537A1 (en) * | 2010-12-22 | 2012-07-11 | Momentive Specialty Chemicals Research Belgium S.A. | glycidyl esters of alpha, alpha branched acids compositions |
| ES2813948T3 (es) | 2011-10-19 | 2021-03-25 | Hexion Res Belgium Sa | Composiciones de resinas de polioléter |
| US9663597B2 (en) | 2011-10-19 | 2017-05-30 | Hexicon Inc. | Acrylic polyol resins compositions |
| BR112014009484A8 (pt) | 2011-10-19 | 2018-02-06 | Hexion Inc | Composição de resinas acrílicas com função hidroxila, processo para preparar uma composição, composição aglutinante, substrato de metal ou de plástico, poliol acrílico, resina de copolímero de poliol acrílico, e, composição de revestimento |
| WO2013072481A1 (de) * | 2011-11-17 | 2013-05-23 | Basf Coatings Gmbh | Glyceroldiester, verfahren zu deren herstellung und deren verwendung in beschichtungsmitteln |
| WO2013075805A2 (en) * | 2011-11-25 | 2013-05-30 | Momentive Specialty Chemicals Research Beigium S.A. | Epoxy compositions |
| CN102924407A (zh) * | 2012-11-30 | 2013-02-13 | 西南化工研究设计院有限公司 | 一种一元羧酸缩水甘油酯的精制方法 |
| KR101650528B1 (ko) * | 2015-04-24 | 2016-08-23 | 대달산업주식회사 | 알파-분지형 지방족 모노카르복시산의 글리시딜 에스테르의 제조 방법 |
| EP3115409A1 (en) * | 2015-07-10 | 2017-01-11 | Hexion Research Belgium SA | Odorless polyester stabilizer compositions |
| KR20170112515A (ko) * | 2016-03-31 | 2017-10-12 | 코오롱인더스트리 주식회사 | 글리시딜에스테르 화합물의 제조방법 |
| WO2018009355A1 (en) | 2016-07-08 | 2018-01-11 | Resinate Materials Group, Inc. | Sustainable polyol blends for high-performance coatings |
| US20190119510A1 (en) * | 2017-10-23 | 2019-04-25 | Hexion Inc. | Glycidyl esters of alpha, alpha branched acids compositions |
| EP3808823A1 (en) * | 2019-10-14 | 2021-04-21 | Hexion Research Belgium SA | Glycidyl esters of alpha, alpha branched acids from renewable sources and formulation thereof |
| CN110683996A (zh) * | 2019-11-01 | 2020-01-14 | 于翔 | 一种叔碳酸缩水甘油酯的制备方法 |
| PH12022552441A1 (en) * | 2020-03-20 | 2024-01-03 | Ingevity South Carolina Llc | Tall oil derived glycidyl esters and process of making the same |
| CN111978502B (zh) * | 2020-08-18 | 2022-04-22 | 北京化工大学常州先进材料研究院 | 一种氨酯油丙烯酸酯光固化树脂及其制备方法 |
| CN117777060B (zh) * | 2023-12-26 | 2024-07-30 | 同宇新材料(广东)股份有限公司 | 一种亚麻油酸缩水甘油酯的制备方法 |
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| WO2009000839A1 (de) * | 2007-06-28 | 2008-12-31 | Basf Se | C10 alkansäureglycidester und ihre verwendung |
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| JP2003171371A (ja) | 2001-12-10 | 2003-06-20 | Yokkaichi Chem Co Ltd | α−モノ分岐飽和脂肪族カルボン酸グリシジルエステルの製造方法 |
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- 2009-06-11 EP EP09075264A patent/EP2261220A1/en not_active Withdrawn
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- 2010-06-02 JP JP2012514373A patent/JP5726180B2/ja active Active
- 2010-06-02 MX MX2011013037A patent/MX2011013037A/es active IP Right Grant
- 2010-06-02 RU RU2014102706/04A patent/RU2560877C2/ru active
- 2010-06-02 EP EP10739480.1A patent/EP2440539B1/en active Active
- 2010-06-02 BR BRPI1013046A patent/BRPI1013046A2/pt not_active Application Discontinuation
- 2010-06-02 KR KR1020127000517A patent/KR101384835B1/ko active Active
- 2010-06-02 CN CN201080025488.3A patent/CN102803242B/zh active Active
- 2010-06-02 US US13/377,470 patent/US8802872B2/en active Active
- 2010-06-02 RU RU2012100273/04A patent/RU2515897C2/ru active
- 2010-06-02 WO PCT/EP2010/003334 patent/WO2010142396A1/en not_active Ceased
- 2010-06-11 TW TW099119175A patent/TWI405758B/zh active
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| SU431162A1 (ru) * | 1972-06-23 | 1974-06-05 | Способ получения глицидиловых эфиров карбоновых кислот | |
| US6433217B1 (en) * | 1998-09-23 | 2002-08-13 | Gerrit Gerardus Rosenbrand | Process for the preparation of glycidylesters of branched carboxylic acids |
| WO2009000839A1 (de) * | 2007-06-28 | 2008-12-31 | Basf Se | C10 alkansäureglycidester und ihre verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102803242B (zh) | 2015-09-23 |
| US8802872B2 (en) | 2014-08-12 |
| EP2440539B1 (en) | 2017-10-04 |
| RU2012100273A (ru) | 2013-07-20 |
| EP2261220A1 (en) | 2010-12-15 |
| JP2012529447A (ja) | 2012-11-22 |
| CN102803242A (zh) | 2012-11-28 |
| MX2011013037A (es) | 2012-02-21 |
| JP5726180B2 (ja) | 2015-05-27 |
| KR101384835B1 (ko) | 2014-04-15 |
| EP2440539A1 (en) | 2012-04-18 |
| US20120095244A1 (en) | 2012-04-19 |
| TW201114751A (en) | 2011-05-01 |
| KR20120016313A (ko) | 2012-02-23 |
| RU2515897C2 (ru) | 2014-05-20 |
| WO2010142396A1 (en) | 2010-12-16 |
| BRPI1013046A2 (pt) | 2015-09-15 |
| RU2014102706A (ru) | 2015-06-27 |
| TWI405758B (zh) | 2013-08-21 |
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